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US4524123A
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Chelatable 4-thienyl imidazole azo dyes, their use in color photographic recording material
Assignee: Agfa Gevaert AG
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Filing: 1984-03-27
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Granted: 1985-06-18
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Expires: 2004-03-27
Abstract
Abstract Azo dyes corresponding to the formula (II): ##STR1## wherein G represents a group capable of forming a 5-membered chelate ring and R 5 represents aryl or a thienyl group, combined with metal ions, in particular copper or nickel ions, to form stable azo dye-metal complexes which have advantageous spectral properties. They are therefore particularly suitable for the production of highly light-fast cyan images, e.g. by the Ink-Jet process, in which they may be used directly in the form of colored inks, or by the dye diffusion transfer process, in which they are released image-wise from corresponding dye-releasers in the course of development and transferred to a dye-absorbent layer.
Inventors
- 👤 Gunther Schenk
- 👤 Peter Bergthaller
- 👤 Holger Heidenreich
- 👤 Gerhard Wolfrum
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 17:34
CPC Classifications
G; G03; G03C; G03C8/00; G03C8/02; G03C8/08; G03C8/10; C; C09; C09B; C09B29/00; C09B29/34; C09B29/36; C09B45/00; C09B45/48
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
234 words
A color photographic recording material for the production of color images by the dye diffusion transfer process, containing, associated with at least one light-sensitive silver halide emulsion layer, a non-diffusible, color-providing compound from which a diffusible azo dye capable of forming complexes with metal ions is released under alkaline development conditions as a function of the development of the silver halide emulsion layer, wherein the improvement comprises the azo dyes corresponds to the following formula (II): ##STR60## wherein R 1 , R 2 , R 3 and R 4 , which may be identical or different, represent H, F, Cl, Br, --CN, --NO 2 , --CF 3 , --OCF 3 , --SCF 3 , alkyl, alkoxy, alkylthio, acylamino, alkylsulfonyl, arylsulfonyl, --CO--X or --SO 2 --Y; or R 3 and R 4 together represent a group for completing a 1,3-oxathiol-S,S-dioxide ring; R 5 represents aryl or a 2-thienyl or 3-thienyl group; R 6 represents hydrogen, halogen or alkyl; G represents a group capable of forming a 5-membered chelate ring; X represents --OH, alkoxy, an amino group optionally substituted by alkyl or aryl, or a cyclic amino group; Y represents H, --OH, an amino group optionally substituted by alkyl or aryl, a cyclic amino group or a group corresponding to the formula --NH --SO 2 --R 7 , and R 7 represents alkyl, aryl, an amino group optionally disubstituted by alkyl, or a cyclic amino group.
Claim 2
Dependent Claim
234 words
A color photographic recording material for the production of color images by the dye diffusion transfer process, containing, associated with at least one light-sensitive silver halide emulsion layer, a non-diffusible, color-providing compound from which a diffusible azo dye capable of forming complexes with metal ions is released under alkaline development conditions as a function of the development of the silver halide emulsion layer, wherein the improvement comprises the azo dyes corresponds to the following formula (II): ##STR60## wherein R 1 , R 2 , R 3 and R 4 , which may be identical or different, represent H, F, Cl, Br, --CN, --NO 2 , --CF 3 , --OCF 3 , --SCF 3 , alkyl, alkoxy, alkylthio, acylamino, alkylsulfonyl, arylsulfonyl, --CO--X or --SO 2 --Y; or R 3 and R 4 together represent a group for completing a 1,3-oxathiol-S,S-dioxide ring; R 5 represents aryl or a 2-thienyl or 3-thienyl group; R 6 represents hydrogen, halogen or alkyl; G represents a group capable of forming a 5-membered chelate ring; X represents --OH, alkoxy, an amino group optionally substituted by alkyl or aryl, or a cyclic amino group; Y represents H, --OH, an amino group optionally substituted by alkyl or aryl, a cyclic amino group or a group corresponding to the formula --NH --SO 2 --R 7 , and R 7 represents alkyl, aryl, an amino group optionally disubstituted by alkyl, or a cyclic amino group.
Claim 3
Independent Claim
249 words
The method of producing a light-stable cyan image by dye diffusion processing of an imagewise exposed color photographic recording material containing, associated with at least one light-sensitive silver halide emulsion layer, a non-diffusible color providing compound while in contact with a supported image receptor layer, the method comprising the step of releasing from said non-diffusible color providing compound under alkaline development conditions a diffusible azo dye corresponding to the following formula ##STR61## wherein R 1 , R 2 , R 3 and R 4 , which may be identical or different, represent H, F, Cl, Br, --CN, --NO 2 , --CF 3 , --OCF 3 , --SCF 3 , alkyl, alkoxy, alkylthio, acylamino, alkylsulfonyl, arylsulfonyl, --CO--X or --SO 2 --Y; or R 3 and R 4 together represent a group for completing a 1,3-oxathiol-S,S-dioxide ring; R 5 represents aryl or a 2-thienyl or 3-thienyl group; R 6 represents hydrogen, halogen or alkyl; G represents a group capable of forming a 5-membered chelate ring; X represents --OH, alkoxy, an amino group optionally substituted by alkyl or aryl, or a cyclic amino group; Y represents H, --OH, an amino group optionally substituted by alkyl or aryl, a cyclic amino group or a group corresponding to the formula --NH--SO 2 --R 7 , and R 7 represents alkyl, aryl, an amino group optionally substituted by alkyl, or a cyclic amino group and transferring at least part of said released azo dye to said image receptor layer and forming complexes with metal ions.
Claim 4
Independent Claim
249 words
The method of producing a light-stable cyan image by dye diffusion processing of an imagewise exposed color photographic recording material containing, associated with at least one light-sensitive silver halide emulsion layer, a non-diffusible color providing compound while in contact with a supported image receptor layer, the method comprising the step of releasing from said non-diffusible color providing compound under alkaline development conditions a diffusible azo dye corresponding to the following formula ##STR61## wherein R 1 , R 2 , R 3 and R 4 , which may be identical or different, represent H, F, Cl, Br, --CN, --NO 2 , --CF 3 , --OCF 3 , --SCF 3 , alkyl, alkoxy, alkylthio, acylamino, alkylsulfonyl, arylsulfonyl, --CO--X or --SO 2 --Y; or R 3 and R 4 together represent a group for completing a 1,3-oxathiol-S,S-dioxide ring; R 5 represents aryl or a 2-thienyl or 3-thienyl group; R 6 represents hydrogen, halogen or alkyl; G represents a group capable of forming a 5-membered chelate ring; X represents --OH, alkoxy, an amino group optionally substituted by alkyl or aryl, or a cyclic amino group; Y represents H, --OH, an amino group optionally substituted by alkyl or aryl, a cyclic amino group or a group corresponding to the formula --NH--SO 2 --R 7 , and R 7 represents alkyl, aryl, an amino group optionally substituted by alkyl, or a cyclic amino group and transferring at least part of said released azo dye to said image receptor layer and forming complexes with metal ions.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-06-17 | 1988-12-17 | 1989-06-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-06-17 | 1992-12-17 | 1993-06-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-06-17 | 1996-12-17 | 1997-06-18 | $7700.00 | Window Closed / Lapsed |